Until recently, few studies have examined the realities of men who choose to pursue careers in professions viewed as 'feminine'. Adopting a qualitative approach, the article seeks to broaden the current state of knowledge on this issue by examining the realities of thirteen male students enrolled in social work at a Chilean university. The respondents participated in individual interviews conducted during the winter semesters of 2014 and 2015. Specifically, the study aims to identify and describe the motivations, obstacles and positive reference points that characterise the trajectories of men who pursue social work studies. The testimonies of participants show that their motivations in studying social work are strongly influenced by a subset of characteristics linked with their life trajectories. In terms of the barriers these men face during their studies and beyond, the results point to historical, cultural and social factors influencing the dimension of gender in relation to social work. The positive reference points that underpin men's decisions to pursue social work studies and careers, despite gender-related obstacles, are linked to their experiences in the university environment. Drawing on participants' testimonies, the authors propose avenues of further research on issues of gender in social work.